Engineering Manager - Data Safety

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they're facing.

• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iterating.

• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.

• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools we use:

• Languages: Python 3, TypeScript

• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js

• Datastores: Postgres, Redis

• Infrastructure: AWS (Fargate, ECS, S3, SageMaker and more), Spark and Kafka

• Monitoring: Datadog, PagerDuty, Sentry

• Version Control: Github

• Vulnerability Management: Snyk, Semgrep

• Cloud Security: Lacework

About this role

Headway's mission is to build a new mental healthcare system that everyone can access. The data we hold to do that is some of the most sensitive there is: what someone said in therapy. Data Safety is the team that makes it possible to learn from that data without putting the people in it at risk.

As Engineering Manager for Data Safety, you'll lead that team. Protecting patient data is Headway's first priority, ahead of any roadmap, and that is not a slogan here: it is the constraint every other team designs around. Your job is to turn that constraint into something people can build on rather than something they route around.

The upside is enormous. With tens of thousands of providers and millions of sessions, Headway holds what is very likely the richest picture of real mental health care anywhere in the world. Remarkably little is known at scale about which care helps whom, and we are sitting on the data that could answer it. The blocker has never been curiosity, it is having a safe way in.

The core of that is de-identification: removing the person from the record while keeping the clinical signal, and getting the method certified so the whole company can rely on it. You'll grow and mentor a team of roughly five to eight engineers, set the roadmap for the pod, and work closely with Security, Legal, Compliance, Data, and the product teams that depend on you.

The bar is high. We have to be able to stand behind how we handle this data to a regulator, to a payer, and to the patient it came from. Get that right and what your team ships sets the ceiling on how much Headway can learn, and on how many people we can help.

Who you are

We're looking for an engineering leader who is pragmatic, product-minded about platform work, and energized by growth. You'll work closely with Engineering Leadership, Security, Legal, and Data to shape how Headway handles its most sensitive data.

In this role you will

• Lead, manage, and grow the Data Safety engineering team

• Own delivery on privacy and compliance commitments, including their audit evidence

• Set the technical and operational roadmap across de-identification, data access tiers, entitlements, and LLM data handling

• Develop your team through weekly 1:1s, mentorship, and direct feedback, and grow a tech-lead layer beneath you

• Partner closely with Security, Privacy and Compliance, Legal, Data Platform, and product pods to move quickly and safely

• Contribute to the broader group and company strategy, not just your own roadmap

Experience we're seeking

• 3+ years of engineering management experience at a high-growth startup or scale-up

• 4+ years of experience as a software engineer, enough to hold technical direction credibly

• A track record of building and leading high-performing teams that delivered business outcomes through technical investment

• A strong product mindset and cross-functional relationships that build trust with users and stakeholders

• Experience shipping under real compliance or audit pressure, with the scope discipline that requires

• Comfort with data platform and privacy systems: access control, data classification, pipelines, and de-identification

• Nice to have: healthcare, financial services, or another regulated, high-trust domain

• Nice to have: HIPAA de-identification, tokenisation, differential privacy, or data governance tooling

• Nice to have: prior experience with Python, React, and AWS infrastructure

You'll love this role if you want to

• Lead the team that decides what the rest of the company can safely learn from its data

• Own commitments the company is accountable for to regulators, auditors, and partners

• Build a tech-lead layer beneath you rather than inherit a finished team

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You'll connect with someone in recruiting so you can learn more about the team, Headway's mission and exciting growth, and we can get a better idea of your background.

• First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experience. You'll also complete an AI Coding round — a collaborative session where we're less focused on syntax and more on how you think through problems and work with AI tools in a technical context.

• Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews and one more technical interview (System Design), leaving you with a fuller picture of what it's like to work at Headway.

• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation:

The expected base pay range for this position is $222,800 - 278,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

Comprehensive benefits:

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.